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The SMSF annually awards scholarships to graduating high school seniors and continuing college students who reside in Middlebury or Southbury, Connecticut. These awards are based on need, academic achievement and community involvement.

The Southbury Middlebury Foundation Grants are funded entirely by donations from local businesses and residents of the two towns. In 2017, awards for graduating seniors totaled $16,700. And an additional $7500 was awarded to continuing college students. Since 1984, Foundation Grants total $597,400.

The SMSF also administers the Delmont and Elfriede Pfeffer Scholarship Fund. The Pfeffer awards were made possible by a memorial endowment from a Heritage Village resident in 1995. The Pfeffer awards are based on academic achievement, community involvement and need. To be considered, applicants must be in the top three deciles (top 30%) of their class, based on Weighted Grade Point Average (GPA). Both GPA and SAT scores will be taken into account in the scoring. The Pfeffer Fund is awarded as four-year scholarships and one-year scholarships. In 2017, Pfeffer Scholarships totaled $187,000. Since 1997, Pfeffer has awarded $2,852,533.